Abstract

In the last few years, the photo-redox process via single-electron transfer (SET) has received substantial attention for the synthesis of targeted organic compounds due to its environmental friendliness and sustainability. Of late visible-light-mediated difunctionalization of alkenes has gained much attention because of its step economy, which allows the consecutive installation of two functional groups across the C=C bond in a single operation. The construction of N-containing compounds has always been important in organic synthesis. Molecules containing C-N bonds are found in many building blocks and are important precursors to other functional groups. Meanwhile, C-N bond formation via the addition of the C=C double bond is gaining prominence. Therefore, considering the influence and synthetic potential of the C-N bond, here we provide a summary of the state of the art on visible-light-driven difunctionalizations of alkene. We hope that the construction of the C-N bond via visible-light-mediated difunctionalization of alkenes will be useful for medicinal and synthetic organic chemists and will inspire further reaction development in this interesting area.

Highlights

  • IntroductionThis visible-light-driven protocol essentially affords a large number of nitrogen centred radicals via a single electron transfer (SET) process or energy transfer process under mild reaction conditions, compared to the traditional radical reactions that use high-energy ultraviolet (UV) light or highly toxic and expensive radical initiators [2]

  • Of late, photo-redox catalysis has been utilized as a flexible and demanding synthetic protocol in the realm of modern organic chemistry due to its environmental friendliness and sustainability [1]

  • This visible-light-driven protocol essentially affords a large number of nitrogen centred radicals via a single electron transfer (SET) process or energy transfer process under mild reaction conditions, compared to the traditional radical reactions that use high-energy ultraviolet (UV) light or highly toxic and expensive radical initiators [2]

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Summary

Introduction

This visible-light-driven protocol essentially affords a large number of nitrogen centred radicals via a single electron transfer (SET) process or energy transfer process under mild reaction conditions, compared to the traditional radical reactions that use high-energy ultraviolet (UV) light or highly toxic and expensive radical initiators [2]. An alkene difunctionalization can introduce two functional groups in a signal operation across the double bond (Figure 1) [4] In this context, the radical-mediated C-N bond formation has Alkenes - Recent Advances, New Perspectives and Applications. This chapter focuses mainly on the difunctionalization of C=C bonds emphasizing the C-N bond formation using visible-light photo-redox catalysis

Photocatalysts
Transition-Metal Complex Photocatalysts
Organic Dye
General mechanism
Ru-catalyzed C-N bond formations
Ir-catalyzed C-N bond formations
Cu and Pd-catalyzed C-N bond formations
Rose Bengal and 9-Fluorenone catalyzed C-N bond formation
Mes-catalyzed C-N bond formation
Eosin-Y-catalyzed C-N bond formation Moon et al in 2019 demonstrated an
Conclusion
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